7 Top Sailing Destinations

By Larry Bleiberg

Sailing Destinations

Whether you’re captaining a dinghy or a yacht, nothing matches the feeling of harnessing the wind and zipping across open waters. Here are top sailing destinations with marinas where you can bring your own boat or easily arrange a charter or rental.


Charleston's Islands, South Carolina

With a top-performing sailing team at the College of Charleston, you can bet to find great conditions in the harbor and off the coast at spots like Folly Beach, Sullivan’s Island and Kiawah Island. Every April, Sperry Charleston Race Week brings in hundreds of captains for the largest keelboat regatta in the Western Hemisphere.

Find a vacation rental on one of Charleston’s Islands here.


Gulf Shores, Alabama

The Alabama Gulf Coast offers multiple options for great sailing with back bays and access directly to the Gulf of Mexico through Perdido Pass on the east and Bon Secour Bay on the west. Popular marinas and docks include Pirate's Cove and Bear Point Marina. Look for regattas on nearby Dauphin Island and Perdido Key.

Find a vacation rental along Alabama’s Gulf Coast here.

Sailing spots

Delaware Beaches

With steady winds and little chop, deep, sheltered Rehoboth Bay can offer visitors near-perfect day-sailing conditions. Others might like warm, shallow Little Assawoman Bay near Fenwick Island. But only the most experienced captains should venture into Delaware Bay, with challenging waters and heavy commercial traffic.

Find a vacation rental in the Delaware Beaches here.


Hilton Head, South Carolina

While well-known for golf, this famed Lowcountry getaway knows how to have fun on the water too. Sailing’s particularly good here in calm and sheltered waters like Calibogue Sound and Broad Creek. Lessons and rentals are plentiful, but many visitors opt for charters with crew who know the area well.

Find a vacation rental in Hilton Head Island here.


Outer Banks, North Carolina

From pirates to explorers, sailors have been plying North Carolina’s waters for centuries. Find your own adventures on the region’s historic sounds, including Albemarle, Currituck, Pamlico and Roanoke, where boaters discover ample scenery and charming anchorages. Each has its own history and character, making for days of fun on the water.

Find a vacation rental in the Outer Banks here.


Northwest Florida

Florida Sailing

From sheltered waters to open sea, the Panhandle welcomes boaters of all experience levels. There’s plenty of room to maneuver in Choctawhatchee Bay, which is four miles wide and 30 miles long. Or scoot under the Destin Bridge and out to the gin-clear waters of the Gulf.

Find a vacation rental on Northwest Florida Beaches here.


Myrtle Beach, South Carolina

Boaters who stick to the Intracoastal Waterway not only find calm waters but also docks at charming seafood restaurants, including The Marina Inn at Grande Dunes, which justifies a stop for a cocktail or meal. It’s also worth heading north of town to Little River, a fun historic fishing village that begs exploring. From there, you can head south to sail from Georgetown, with its gorgeous plantations.

Find a vacation rental in Myrtle Beach here.


Freelance journalist Larry Bleiberg is the former Travel Editor of the Dallas Morning News, and Coastal Living magazine. He has co-authored four guidebooks, including three for National Geographic.



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